2589-72-2

Usage

Uses

Used in Chemical Synthesis:
4-(Hydroxyphenyl)-1-heptanone is used as an intermediate in the synthesis of various organic compounds, particularly those with potential applications in pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification, making it a valuable building block in the development of new molecules.
Used in Research and Development:
In the field of scientific research, 4-(Hydroxyphenyl)-1-heptanone serves as a model compound for studying the properties and reactivity of ketones and phenols. It is used to investigate the effects of structural variations on the chemical behavior of molecules, contributing to the understanding of fundamental organic chemistry principles.
Used in Material Science:
4-(Hydroxyphenyl)-1-heptanone may be employed as a component in the formulation of advanced materials, such as polymers, coatings, and adhesives. Its chemical structure can influence the physical and mechanical properties of these materials, potentially leading to the development of novel products with improved performance characteristics.
Used in Analytical Chemistry:
As a reference compound, 4-(Hydroxyphenyl)-1-heptanone can be used in analytical chemistry for the calibration of instruments and the development of analytical methods. Its distinct spectral features and reactivity can aid in the accurate identification and quantification of similar compounds in complex mixtures.

InChI:InChI=1/C12H16O2/c1-2-3-4-5-12(14)10-6-8-11(13)9-7-10/h6-9,13H,2-5H2,1H3

Upstream product

• 142-62-1 hexanoic acid 
• 108-95-2 phenol 
• 7780-16-7 phenyl hexanoate 
• 142-61-0 Hexanoyl chloride 
• 628-71-7 1-Heptyne 
• 106-51-4 p-benzoquinone 
• 769936-20-1 4-(2-pentyl-[1,3]dithian-2-yl)-phenol 

Downstream Products

• 101720-12-1 isonicotinic acid-[1-(4-hydroxy-phenyl)-hexylidenehydrazide] 
• 121384-26-7 1-(4-hydroxyphenyl)-1-hexanol 
• 20683-49-2 1-(3,5-dibromo-4-hydroxy-phenyl)-hexan-1-one 
• 17404-20-5 4-<1-Pentyl-octen-(1)-yl>-phenol 
• 6397-82-6 4'-methoxyhexanophenone 
• 2446-69-7 p-hexylphenol 
• 80417-32-9 4-Butoxy-benzoic acid 4-hexanoyl-phenyl ester 
• 15234-77-2 2-(4-Hexanoyl-phenoxy)-2-methyl-propionic acid 
• 15234-75-0 (4-Hexanoyl-phenoxy)-acetic acid 
• 769936-20-1 4-(2-pentyl-[1,3]dithian-2-yl)-phenol 
• 769936-21-2 2-(4-methoxy-phenyl)-2-pentyl-[1,3]dithiane 
• 360553-72-6 1-[4-(3-piperazin-1-yl-propoxy)-phenyl]-hexan-1-one 
• 18102-14-2 5-hexylsalicylaldehyde 
• 80407-01-8 4-Hexylcyclohexanol 

Relevant academic research and scientific papers

Visible Light-Mediated [2 + 2] Cycloaddition Reactions of 1,4-Quinones and Terminal Alkynes

A single-step synthesis of 4-hydroxy-functionalized bi-aryl and aryl/alkyl ketones via oxidative coupling of terminal alkynes with benzoquinones is reported. Furthermore, with naphthoquinones, owing to the cross-resonance of carbonyl with the aromatic ring, alkene-alkyne cycloaddition is more favored to give four-membered carbocyclic adducts, thereby precluding the requirement of preactivated alkynes.

Synthesis of the ortho / meta / para isomers of relevant pharmaceutical compounds by coupling a Sonogashira reaction with a regioselective hydration

Aryl ketones substituted in ortho, meta, and para position are prepared by a palladium-catalyzed Sonogashira reaction followed by a regioselective hydration of the so-formed alkyne with triflimidic acid or a gold catalyst, under catalytic conditions. This methodology opens a way to obtain substituted aryl alkyl ketones from readily available starting materials, haloarenes, and terminal alkynes. The syntheses of the different regioisomers of haloperidol, melperone, pipamperone, and ibuprofen are presented. Structure-activity relationships for these compounds are studied with dopaminergic and cyclooxigenase binding assays.

Synthesis, biochemical evaluation and rationalisation of a series of 3,5- dibromo derivatives of 4-hydroxyphenyl ketone-based compounds as probes of the active site of type 3 of 17β-hydroxysteroid dehydrogenase (17β-hsd3) and the role of hydrogen bonding interaction in the inhibition of 17β-HSD3

We report the synthesis, evaluation and rationalisation of the inhibitory activity of a series of 3,5-dibromo derivatives of 4-hydroxyphenyl ketone as probes of the active site of the type 3 of 17β-hydroxysteroid dehydrogenase (17β-HSD3). The results support the important role of hydrogen bonding interaction in the inhibition of 17β-HSD3.

Comparisons of O-acylation and Friedel-Crafts acylation of phenols and acyl chlorides and Fries rearrangement of phenyl esters in trifluoromethanesulfonic acid: Effective synthesis of optically active homotyrosines

Reactions involving phenol derivatives and acyl chlorides have to be controlled for competitive O-acylations and C-acylations (Friedel-Crafts acylations and Fries rearrangements) in acidic condition. The extent for these reactions in trifluoromethanesulfonic acid (TfOH), which is used as catalyst and solvent, is examined. Although diluted TfOH was needed for effective O-acylation, concentrated TfOH was required for effective C-acylations in mild condition. These results have been applied to the novel synthesis of homotyrosine derivatives. Both Fries rearrangement of N-TFA-Asp(OBn)-OMe and Friedel-Crafts acylation of phenol with N-TFA-Asp(Cl)-OMe in TfOH afforded the homotyrosine skeleton, followed by reduction and deprotection afforded homotyrosines maintaining stereochemistry of Asp as an optically pure form.

Synthesis and biochemical evaluation of a series of trifluoromethanesulfonate derivatives of 4 hydroxyphenyl ketones - Probes of the active site of type 1 and 3 of the 17β-hydroxysteroid dehydrogenase family of enzymes

In an effort to aid the design of 'dual-inhibitors' of types 1 and 3 of the 17β-hydroxysteroid dehydrogenase (17β-HSD), we report the synthesis, biochemical evaluation and rationalisation of the inhibitory activity of trifluoromethanesulfonate derivatives of 4-hydroxyphenyl ketone-based compounds which were found to be weak inhibitors of types 1 and 3.

Synthesis of a series of novel 2,4,5-trisubstituted selenazole compounds as potential PLTP inhibitors

Based on a homology-modeled structure of PLTP and characteristic structural features of reported cholesteryl ester transfer protein (CETP) inhibitors, we designed and synthesized a novel series of 2,4,5-trisubstituted selenazole compounds. Biological evaluation reveals that compounds 12 and 17 exhibit favorable PLTP activity, and their IC50s are 8 μM and 10 μM, respectively.

Synthesis, biochemical evaluation and rationalisation of the inhibitory activity of a series of 4-hydroxyphenyl ketones as potential inhibitors of 17β-hydroxysteroid dehydrogenase type 3 (17β-HSD3)

We report the preliminary results of the synthesis and biochemical evaluation of a number of 4-hydroxyphenyl ketones as inhibitors of the isozyme of the enzyme 17β-hydroxysteroid dehydrogenase (17β-HSD) responsible for the conversion of androstenedione (AD) to testosterone (T), more specifically type 3 (17β-HSD3). The results of our study suggest that we have synthesised compounds which are, in general, potent inhibitors of 17β-HSD3, in particular, we discovered that 1-(4-hydroxy-phenyl)-nonan-1-one (8) was the most potent (IC50 = 2.86 ± 0.03 μM). We have therefore provided good lead compounds in the synthesis of novel non-steroidal inhibitors of 17β-HSD3.

Oxidative deprotection of 1,3-dithiane group using NaClO2 and NaH2PO4 in aqueous methanol

The 1,3-dithiane group was oxidatively deprotected under the conditions of sodium chlorite, sodium dihydrogenphosphate, and 2-methyl-2-butene in 3:1 methanol-water at room temperature in good yield.

Tilt Angle Variation as a Function of Chain Length and Temperature in the Smectic C Phases of p,Alkoxyphenyl-p,Alkoxybenzoates

The variation of the tilt angle with temperature in the smectic C phase has generally been shown to be non-existent or very slow for compounds or mixtures with the nematic-smectic C transition, while in the case of systems with the smectic A-smectic C transition, a relation between the steepness of this variation, near the transition, and the width of the smectic A domain has been observed.In this work, the variation of tilt angle in the smectic C phase is described for p-alkoxyphenyl-p-alkoxybenzoate homologous series, for which the evolution of polymorphism can be controlled systematically, by varying stepwise the length of the aliphatic chains, and for which large domains can be obtained for each type of phase sequence, nematic-, smectic A- and isotropic-smectic C.After completing the discussion made previously on the incidence of chain length on polymorphism, we confirm that the variation of tilt angle with temperature is slowest for compounds with intermediate chain lengths corresponding to the largest smectic A temperature range; this variation becomes continuously steeper when the smectic A domain becomes narrow.In addition, we show that the same description can be extended to the other types of phase sequences, by using the hypothesis of a virtual smectic A-smectic C transition above the observed nematic- or isotropic-smectic C transition.In fact, short chain lengths for homologues with a nematic/smectic C transition, or long chain lengths for homologues with an isotropic/smectic C transition, lead to an increase of the tilt angle at the phase transition and to a decrease of the amplitude of its variation with temperature; in our description, this behaviour corresponds to an increase of the temperature range between the real and virtual transitions.As a consequence, the homologues with very short and very long chain lengths show a quasi temperature-independent tilt angle, while the other homologues present a tilt angle variation similar to that observed for compounds exhibiting a smectic C/smectic A transition.This feature indicates that there is no need to distinguish between different types of smectic C phase.

Aliphatic Liquid Crystals, 2. Some Nematic Derivatives of all-trans-Perhydrophenanthrene

A stereoselective synthesis of the all-trans-7-alkylperhydro-2-phenanthrenols 15a-f in 11 steps and 28 liquid crystalline esters 16 of 15a-f are described, additionally some further derivatives of 7-alkylperhydro-2-phenanthrenol.An X-ray structure analysis of ester 16ec is reported.